This invention generally pertains to heterocyclic carbon compounds having drug and bio-affecting properties and to their preparation and use. In particular, the invention is concerned with disubstituted cycloalkanyl and cycloalkenyl derivatives wherein one substituent moiety is an indol-3-yl-5-nitrile group and the other moiety is an alkyl, aryl or heteroaryl, e.g. pyridinyl, amino group. These compounds are potent serotonin uptake inhibitors which renders them useful as antidepressant agents.
Several series of compounds comprising a central cycloalkanyl or cycloalkenyl ring linked both to an indole group and to an amine containing functionality have been reported.
Smith, et al. in U.S. Pat. No. 4,954,502 disclosed compounds of formula (i) having antidepressant properties. In these compounds R.sup.3 and R.sup.4 are ##STR2## not nitrile functionalities but A was, inter alia, a 5 to 7 carbon cycloalkanyl or cycloalkenyl ring.
Wise, et al. in U.S. Pat. No. 5,124,332 described compounds of formula (ii) as being useful for central nervous system disorders, including depression. ##STR3## In formula (ii), R.sup.3 was not a nitrile moiety and Y could be C or N.
Mattson, et al. in EP 0560669A disclosed antipsychotic agents of formula (iii). ##STR4## In formula (iii), R was not a nitrile functionality and Y could be C or N.
Caprathe, et al. in WO 93/10092 disclosed a series of compounds, including those of formula (iv), as dopaminergic ##STR5## agents useful in treating psychosis and CNS disorders involving disturbances in dopamine transmission.
Of less relevance are the neuroleptic and antiemetic compounds of formula (v) disclosed in Fr 2,458,550 for RousseI-Uclaf. ##STR6## In formula (v), X is, inter alia, a phenalkyl group.
The foregoing references do not teach nor suggest the specific combination of structural variations that comprise the compounds of the present invention and their use as antidepressant agents.